Preparation of Pyrazolo3,4-bpyridines and - Villeurbanne, France - ICBMS INSA Lyon

Description

Preparation of pyrazolo[3,4-b]pyridines and integration in late-stage functionalization:

• Réf
  ABG-121419
• Sujet de Thèse 19/03/2024
• Contrat doctoral
• ICBMS INSA Lyon
• Lieu de travail
• Villeurbanne
• Auvergne-RhôneAlpes
• France
• Intitulé du sujet
• Preparation of pyrazolo[3,4b]pyridines and integration in latestage functionalization
• Champs scientifiques
• Chimie

• Mots clés

• Heterocyclic chemistry, Catalysis, Late stage functionnalization, Borrowing Hydrogen
  Description du sujet:

Preparation of pyrazolo[3,4-_b_
]pyridines and integration in late-stage functionalization

• A multitude of aromatic heterocycles have a bicyclic nitrogen structure. Among these, the pyridine[_b_]bicyclic unit is extremely common, and consists of a pyridine fused to another aromatic ring. The pyrazolo[3,4_b_]pyridine ring has a pyridine ring attached to a pyrazole. This motif is present in a multitude of compounds with biological activity, such as anxiolytics, antifungals, antileishmaniases and even as antiinfluenza agents. For our part, in collaboration with the Microbiology, Adaptation and Pathogenesis team (UMR5240), we have been able to show that certain molecules have bactericidal or bacteriostatic properties.
• Finally, functionalization in C3 position will be envisioned using the
  borrowing hydrogen (BH) methodology with various primary and secondary alcohols. This onepot transformation has emerged as an attractive strategy for the construction of novel C-C bonds from an alcohol and a Cnucleophile.[2] A first step of catalytic dehydrogenation converts an unreactive alcohol into the corresponding carbonyl. Subsequent aldol condensation with a Cnucleophile gives the corresponding α,βunsaturated ketone which upon hydrogenation affords the expected Calkylated compound. We thus propose to take advantage of the pyrazolopyridine as a novel Cnucleophile.
  A wide range of latestage transformations will be evaluated in the framework of this PhD program and the library of
  compounds will be integrated in the Chimiothèque Nationale for biological screening.

- [1] Lavrard, H.; Popowycz, F. _Eur J Org Chem_
2017, _2017_,
- [2] François, J. ; Rio, J. ; Jeanneau, E. ; Perrin, M.È. L. ; Jacolot, M. ; Payard, P.A. ; Popowycz, F. _Org. Chem. Front._
2023, _10_,


Prise de fonction:

• 01/10/2024
  Nature du financement:
• Contrat doctoral

Précisions sur le financement:


Présentation établissement et labo d'accueil:

• ICBMS INSA Lyon

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Site web:


Intitulé du doctorat:

• Doctorat de Chimie
  Pays d'obtention du doctorat:
• FranceWe are looking for a highly motivated person with a Master degree in organic chemistry and good knowledge of analytical methods dedicated to organic molecules (NMR, MS). Experience in organometallic chemistry will be appreciated but is not mandatory.

A good motivation to learn, communication skills, curiosity, and good team spirit are also among important qualities. Good knowledge of English is also important.

**- 19/04/2024